DE216668C - Process for the representation of burgundy to violet vat dyes of the anthracene series - Google Patents
Process for the representation of burgundy to violet vat dyes of the anthracene seriesInfo
- Publication number
- DE216668C DE216668C DE1908216668D DE216668DA DE216668C DE 216668 C DE216668 C DE 216668C DE 1908216668 D DE1908216668 D DE 1908216668D DE 216668D A DE216668D A DE 216668DA DE 216668 C DE216668 C DE 216668C
- Authority
- DE
- Germany
- Prior art keywords
- representation
- burgundy
- violet
- vat dyes
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000001454 anthracenes Chemical class 0.000 title claims description 3
- 239000000984 vat dye Substances 0.000 title claims 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- NXDLHZSMNGRDTD-UHFFFAOYSA-N 1-(aminomethoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2OCN NXDLHZSMNGRDTD-UHFFFAOYSA-N 0.000 description 9
- 239000000975 dye Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 244000172533 Viola sororia Species 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 2
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 244000154870 Viola adunca Species 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- -1 halogen anthraquinones Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 1
- ITXBUJHIGBXXKK-UHFFFAOYSA-N 1-bromo-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2OC ITXBUJHIGBXXKK-UHFFFAOYSA-N 0.000 description 1
- 241000031711 Cytophagaceae Species 0.000 description 1
- 241000394591 Hybanthus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical class [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 216668 KLASSE 22 h. GRUPPE- JVl 216668 CLASS 22 h. GROUP
der Anthracenreihe.the anthracene series.
Zusatz zum Patente 162824 vom 30. Oktober 1903.Addendum to patent 162824 of October 30, 1903.
Patentiert im Deutschen Reiche vom 8. November 1908 ab. Längste Dauer: 29.Oktober 1918.Patented in the German Empire on November 8, 1908. Longest duration: October 29, 1918.
Kondensiert man nach dem Verfahren des Hauptpätentes ρ - Aminoalkoxyanthrachinone mit Halogen anthrachinon en oder p-Halogenalkoxyanthrachinone mit Aminoanthrachinonen, so gelangt man zu neuen Farbstoffen, die Baumwolle in schönen, echten, bordeauxfarbenen bis violetten Nuancen anfärben, wie sie in gleicher Nuance und Echtheit bisher mit anderen Farbstoffen dieser Gruppe nicht erzielt wurden. So färben die aus p-substituierten Alkoxyanthrachinonen erhaltenen Dianthrachinonyle z. B. wesentlich blaustichiger als die in der französischen Patentschrift 390677 beschriebenen, aus heteronuclearen Derivaten der Alkoxyanthrachinone erhältlichen Produkte.If ρ - aminoalkoxyanthraquinones are condensed according to the method of the main patent with halogen anthraquinones or p-haloalkoxyanthraquinones with aminoanthraquinones, this is how you get to new dyes, cotton in beautiful, genuine, burgundy colors to dye violet nuances in a way that has not been possible before with other dyes of this group in the same shade and authenticity were achieved. This is how the dianthraquinonyls obtained from p-substituted alkoxyanthraquinones color z. B. much more bluish than that in French patent 390677 described products obtainable from heteronuclear derivatives of alkoxyanthraquinones.
30 Teile 1 · 4-Aminomethoxyanthrachinon werden mit 30 Teilen ß-Chloranthrachinon, 4 Teilen Kupferchlorür, 25 Teilen entwässertem Natriumacetat und 300 Teilen Naphtalin etwa 6 Stunden gekocht. Durch Zusatz von Solventnaphta wird der Farbstoff vollständig abgeschieden. Nach dem Abkühlen auf 40 bis 50° wird abgesaugt, mit Solventnaphta, Eisessig, Salzsäure und Wasser gewaschen und getrocknet. Man erhält so in sehr guter Ausbeute ein dunkelbordeauxfarbenes Pulver.30 parts of 1 · 4-aminomethoxyanthraquinone are mixed with 30 parts of ß-chloroanthraquinone, 4 parts Copper chloride, 25 parts of dehydrated sodium acetate, and 300 parts of naphthalene approximately Cooked for 6 hours. The dye is completely deposited by adding solvent naphtha. After cooling to 40 to 50 °, it is filtered off with suction, washed with solvent naphtha, glacial acetic acid, hydrochloric acid and water and dried. A dark claret-colored powder is obtained in this way in a very good yield.
Kondensiert man wie in Beispiel 1 30 Teile ι · 4-Brommethoxyanthrachinon mit 23 Teilen 2-Aminoanthrachinon, so erhält man das gleiche Produkt wie nach Beispiel 1.30 parts are condensed as in Example 1 ι · 4-Bromomethoxyanthraquinone with 23 parts 2-Aminoanthraquinone, the same product as in Example 1 is obtained.
Kondensiert man in der gleichen Weise wie in Beispiel 1 50 Teile 1 · 4-Äminomethoxyanthrachinon mit 25 Teilen 2 · 6-Dichloranthrachinon, so erhält man ein braunviolettes Pulver, welches das Kondensationsprodukt aus 2 Molekülen ι · 4 - Aminomethoxyanthrachinon mit ι Molekül 2 · 6 - Dichloranthrachinon darstellt.50 parts of 1x4-aminomethoxyanthraquinone are condensed in the same manner as in Example 1 with 25 parts of 2 · 6-dichloroanthraquinone, a brown-violet powder is obtained which the condensation product of 2 molecules ι · 4 - aminomethoxyanthraquinone with ι Molecule 2 · 6 - represents dichloroanthraquinone.
Werden in der in Beispiel 1 angegebenen Weise 50 Teile 1 · 4 Aminomethoxyanthrachinon mit 25 Teilen 2 ^-Dichloranthrachinon kondensiert, so erhält man ein dunkelviolettes Pulver. Der Farbstoff ist das Kondensationsprodukt aus 2 Molekülen 1 · 4-Aminomethoxyanthrachinon mit ι Molekül 2 · 7-Dichloranthrachinon. Are in the manner indicated in Example 1 50 parts of 1 · 4 aminomethoxyanthraquinone condensed with 25 parts of 2 ^ -dichloroanthraquinone, a dark purple color is obtained Powder. The dye is the condensation product of 2 molecules of 1 · 4-aminomethoxyanthraquinone with ι molecule 2 · 7-dichloroanthraquinone.
Analoge schöne und echte Produkte erhält man durch Kondensation anderer p-Methoxyanthrachinonderivate. Analogous beautiful and genuine products are obtained by condensation of other p-methoxyanthraquinone derivatives.
3535
4040
4545
5555
Die Eigenschaften dieser und einiger anderer analog erhaltener Produkte sind in nachstehender Tabelle aufgeführt.The properties of these and some other products obtained analogously are shown below Table listed.
Produkt aus5
Product from
in konzentrierter
Schwefelsäuresolution
in more concentrated
sulfuric acid
der Substanz
in Pastecolour
the substance
in paste
auf ungeheizte
Baumwollecoloring
on unheated
cotton
-j- 2-Chloranthrachinon
bzw. ■
ι ■ 4-Methoxybromanthrachinon
+ 2-Aminoanthrachinonίο ι. 4-aminomethoxyanthraquinone
-j- 2-chloroanthraquinone
or ■
ι ■ 4-methoxybromoanthraquinone
+ 2-aminoanthraquinone
+ ι Molekül 2 · 6-Dichloranthrachinon! 5 2 molecules ι · 4-aminomethoxyanthraquinone
+ ι molecule 2 · 6-dichloroanthraquinone
+ ι Molekül 2 · 7-Dichloranthrachinon2 molecules of 1 · 4-aminomethoxyanthraquinone
+ ι molecule 2 · 7-dichloroanthraquinone
+ 1 · ö-Methoxychloranthrachinon 20 ι · 4-aminomethoxyanthraquinone
+ 1 · δ-methoxychloranthraquinone
+ ι · ö-Methylaminochloranthrachinon4-aminomethoxyanthraquinone
+ ι · ö-Methylaminochloranthraquinone
ι · S-Dimethoxy^-aminoanthrachinon
-f- 2-Chloranthrachinonever
ι · S-dimethoxy ^ -aminoanthraquinone
-f- 2-chloroanthraquinone
+ 2 Moleküle 2-Chloranthrachinon
onι · 8-Dimethoxy-4 · 5-diaminoanthraquinone
+ 2 molecules of 2-chloroanthraquinone
on
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE162824T | 1903-10-30 | ||
| DE216668T | 1908-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE216668C true DE216668C (en) | 1909-11-29 |
Family
ID=43558102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1908216668D Expired DE216668C (en) | 1903-10-30 | 1908-11-08 | Process for the representation of burgundy to violet vat dyes of the anthracene series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE216668C (en) |
-
1908
- 1908-11-08 DE DE1908216668D patent/DE216668C/en not_active Expired
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